Juan Ponce de Leon poked around this coast in 1513 and claimed the land for Spain. Afterwards both the French and Spanish attempted colonization in Florida but nothing took hold until 1565 when Spanish King Phillip II dispatched Pedro Menendez de Aviles to establish a base from which to attack the French. Menendex arrived in Florida on the feast day of St. Augustine of Hippo and named his landing site after the saint. From that day on the town has been continuously occupied, establishing St. Augustine as the oldest city in America.

It was not without struggle. The town was sacked by pirates and under regular threat or attack, especially as the English colonies began spreading down the American coast in the 1600s. As such St. Augustine evolved as a military post more than as an economic and cultural center. After the town was attacked and plundered by English privateer Robert Searle in 1688 the Spanish began in 1672 the construction of a more secure fortification, the Castillo de San Marcos, which still stands today as the nation’s oldest fort.

As part of the Treaty of Paris ending the French and Indian War in 1763 the British received Florida in exchange for relinquishing control of occupied Cuba. Almost all of the more than 3,000 Spaniards sailed away, mostly to Cuba. The British were energetic stewards but the territory was ceded back to Spain by the United States in 1783 as recognition for their assistance in the American Revolution. Many of the St. Augustine exiles returned but by this time Spain was struggling to retain its distant colonies and it was only a matter of time before Florida would become a United States territory. It happened peaceably in 1821 by way of the Adams-Onis Treaty.

St. Augustine’s military heritage continued under American rule. The town played a role in the Seminole Wars and the War Between the States and the old fort was a military prison during the Spanish-American War. Only in 1898, after more than 200 years as an active fort under five different flags was the Castillo de San Marcos deactivated.

Henry Flagler, a failed salt miner, went into the oil refining business with John D. Rockefeller in 1867 and they built the biggest business empire in the world. Although Rockefeller’s is the name most associated with Standard Oil, he always gave the credit to its success to Flagler. On a wedding trip to Florida with his second wife in 1881 the Flaglers visited St. Augustine where they were charmed with the town’s Old World Spanish flavor. In short order Flagler gave up day-to-day operations at Standard Oil and set about developing St. Augustine as “the Newport of the South.” His vision would soon extend down the peninsula, however, extending his railroad and development all the way to Key West by 1912. What Flagler started in St. Augustine with a 540-room hotel would grow into a personal bet of $50 million on the future of Florida.

Over the years St. Augustine has tried to maintain that Spanish charm that bewitched Henry Flagler 130 years ago and to see how they’ve succeeded we will begin at the busy Visitor Center... 

BEGIN BY WALKING OVER TO THE PATIO ON THE ORANGE STREET SIDE OF THE VISITOR CENTER.

1.
Fuente de los Canos de San Francisco
St. Augustine Visitor’s Info Center
10 South Castillo Drive

The Spanish town from which St. Augustine founder Pedro Menendez hailed, Aviles, has been a sister city since the early 20th century. Among the gifts exchanged is this replica of six faces that have serve as water spouts for the municipal fountain in the San Francisco neighborhood since the 1500s.  

NEXT TO THE FOUNTAIN REPLICA IS...

2.
Zero Milestone Marker
St. Augustine Visitor’s Info Center
10 South Castillo Drive

The “Zero Milestone Marker of the Old Spanish Trail” conjures up images of conquistadores on horseback setting off down a sandy trail to seek riches 3000 miles away. Actually it dates to the early days of the automobile when towns lobbied planners of long-distance roads to have new highways pass through their town. After Mobile, Alabama was bypassed by the Dixie Highway in 1915 the Rotary Club of Mobile began promoting a route that could take drivers from the Atlantic Ocean at St. Augustine all the way to the Pacific Ocean at San Diego, by way of Mobile. The roads, more or less, were ready by 1929 and the route was given the romantic identity of the “Old Spanish Trail.” Along the way it passed through towns of Spanish origin but the first ones to travel it were motorists, not Spanish explorers. This six-foot coquina rock sphere was unveiled during the celebration of the route.

WALK OVER TOWARDS THE WATER TO CASTILLO DRIVE. DO NOT CROSS THE STREET. TURN RIGHT. ON YOU RIGHT IS...

3.
Huguenot Cemetery
northwest corner of Castillo Drive and Orange Street

In front of the Visitor Center, behind a low coquina wall, is a public burying ground that was set aside for non-Catholics during an outbreak of yellow fever in 1821. Victims of the epidemic may have been buried in mass graves by overwhelmed officials. Prior to the formation of this cemetery, Protestants had been buried on Anastasia Island, a practice which became untenable. There are probably no Hugenots interred here and the graveyard has been owned and maintained by the Protestant church since 1832. Burials ended in 1884 and the site became overgrown before restoration began in 1979; the grounds are not open for exploration.

CAREFULLY CROSS THE STREET ONTO THE GROUNDS OF THE CASTILLO DE SAN MARCOS, A NATIONAL MONUMENT...

4.
Castillo de San Marcos
1 South Castillo Drive at Matanzas Bay

This is the oldest masonry fort in the United States, constructed of soft shellrock coquina. Construction began in 1672 and was mostly completed by 1695, although modifications would continue until 1756. With outer walls 12 feet thick at the base and space onthe diamond-shaped bastions for over 70 cannon, the Castillo de San Marcos stood at the northernmost point of Spain’s claims in the New World, the largest empire ever created. It replaced the series of wooden forts that had defended St. Augustine for more than a century. When the British were her it became St. Marks and after the Americans bought Florida it was Fort Marion, named in honor of South Carolina Revolutionary patriot Francis Marion. 

WHEN YOU ARE THROUGH EXPLORING THE FORT, RE-CROSS CASTILLO DRIVE TO THE GATE AT THE HEAD OF ST. GEORGE STREET.

5.
Old City Gate
head of St. George Street at Orange Street

In 1704, the Spanish began construction of the Cubo line, an earthen wall backed by cannon-ball absorbing palmetto logs. The wall stretched from the Castillo de San Marcos on Matanzas Bay across to the San Sebastian River, protecting the northern boundary of the town. At intervals were square redoubts such as the re-created San Domingo Redoubt in front of the Visitor Center. The walls would eventually come to enclose the entire city and effective they were - St. Augustine would never be conquered after they were built. Access was through this gate, since 1808 constructed of square coquina pylons. Attached to the gate was a drawbridge over the moat that fronted the Cubo line.

WALK THROUGH THE GATE AND DOWN THE PEDESTRIAN-ONLY ST. GEORGE STREET. MORE THAN 50 STRUCTURES HAVE BEEN RESTORED ON THIS ANCIENT LANE, NOW SERVING AS CRAFT SHOPS, EATERIES AND MUSEUMS.

6.
Oldest Wooden Schoolhouse
14 St. George Street

Constructed of red cedar and cypress and put together with wooden pegs and handmade nails this building, which also served as a guardhouse during the Seminole Wars, lays claim to being the oldest wooden schoolhouse in the United States. the schoolmaster and his family lived cozily upstairs, above the small classroom. Inside the floors are made of tabby, a common seaside construction material made of crushed oyster shells and lime.

7.
Colonial Spanish Quarter
29 St. George Street

Behind the Triay House is a reconstructed work area where blacksmiths once forged nails and carpenters fashioned pegs from cedar logs. It now operates as a living history museum.

8.
Casa Avero
41 St. George Street 

A colonizing ship of 500 Greeks sailed from Smyrna, Crete and Mani to the New World in 1768. After stopping in St. Augustine for fresh supplies they continued ten miles south to establish the settlement of New Smyrna. The colony failed and ten years later the Greek survivors sough refuge inside the walls of St. Augustine. They gathered in the Casa Avero for worship where Their St. Photis Chapel is today considered the National GreekOrthodox Shrine honoring the first permanent settlement of Greeks on the North American continent.

9.
Rodriguez-Avero-Sanchez House
52 St. George Street

This is an original house on St. George Street, the core of which was begun in 1760 when Fernando Rodriguez, a sergeant in the Castillo de San Marcos garrison built a wooden house here. Antonia Avero inherited the property but fled to Cuba when the British occupation began in 1763. When the British departed in 1783 Avero returned but was unable to reclaim her house which was sold at public auction to Juan Sanchez in 1791. Sanchez built the coquina-block portion of the house, listed on the National Register of Historic Places, that was restored in the 1960s.

10.
Sanchez House
115 St. George Street

Here is a restoration of a coquina and masonry house erected by Francisco Xavier Sanchez, a merchant, planter and one of the richest and most influential men in Florida. Sanchez was 17 when the British assumed control of St. Augustine but he decided to stay and live under English rule. As his business career progressed Snachez worked to undermine the British authority, so much so that in 1783 he was accused by the British Governor Patrick Tonyn of committing a long series of trespasses against the British. The British, however, would be soon to depart. In 1787 when Sanchez was 41 years old he married Maria Carmon Hill of Charleston, South Carolina, then 16. this house was constructed around the time of his death in 1807.   

11.
Pena-Peck House
143 St. George Street

This house began life as the residence of the Spanish Royal Treasurer, Juan Esteban de Pena, in 1750. In 1767, John Moultrie of South Carolina, who held a medical degree from Edinburgh University in Scotland but spent his time in America growing the best indigo in the colonies, moved to Florida as British Lieutenant Governor. When he wasn’t tending to his plantations he stayed in this house. In 1837 Dr. Seth S. Peck of Connecticut purchased the house and rebuilt it on the original native coquina walls and adding a frame second-story. He had little time to enjoy the residence as he died during the Yellow Fever epidemic of 1841. The house would remain in the Peck family, however, for almost a century. It was willed to the City in 1931 and restored in 1968.

AT CATHEDRAL PLACE TURN LEFT, WALKING TOWARDS THE WATER.

12.
Cathedral-Basilica of St. Augustine
38 Cathedral Place

This parish dates its beginnings to within 48 hours of Don Pedro Menendez’s landing on September 8, 1565 when a celebratory Mass was held. After Britain ceded Florida back to Spain in 1784 the Spanish crown ordered the construction of a new parish church. The cornerstone for this cathedral was laid in 1793 and the first Mass conducted on December 8, 1797. Following a fire in 1887 the building was restored and a Spanish Renaissance bell tower added next door. James Renwick, Jr., an architect famous for his work at the Smithsonian Institute in Washington and St. Patrick’s Cathedral in New York City, drew up the plans for the bell tower. Then in his seventies, Renwick was living on Anastasia Island across the Matanzas Bay at the time. 

13. 
Wells Fargo
24 Cathedral Place

This is the first - and last - “skyscraper” built in St. Augustine. The six-story Mediterranean-flavored building with a mezzanine was constructed in 1928 for the First National Bank from plans drawn from F.A. Hollingsworth, a Virginian architect who came to St. Augustine to work for the Florida East Coast Railway and stayed to open his own office in 1922. First National Bank did not make it out of the Depression but the building, with its original vault and marble lobby, has done duty as a bank ever since, save for a few fallow years.

14.
American Legion Post 37
1 Anderson Circle at Avenida Menendez

Charles F. Hamblen was a shopkeeper in Main who moved to St. Augustine in 1875 and established a small grocery. He shifted into hardware which proved extremely profitable and eventually moved into the warehouse on Artillery Street where the Oldest Store Museum is today. In 1886 Hamblen erected an eclectic Victorian frame mansion on this bayfront location that he called Blenmore. Charles Hamblen passed away here on December 29, 1920 at the age of 84, leaving his home to an as yet unformed men’s social club. the Hamblen Club operated here, with a Mediterranean style makeover by celebrated Jacksonville architects Harold F. Saxelbye and William Mulford Marsh, until 1940 when the American Legion moved in on lease. 

15.
Bridge of Lions
Cathedral Place at Matanzas River

The first attempt to span the Matazanas River to Anastasia Island resulted in a wooden bridge in 1895. This steel bascule bridge was begun in 1925 and was finished two years and a million dollars later. With its gracefully arched girders and Mediterranean-style bascule towers, the 1,574-foot bridge was acclaimed as one of the most beautiful in the South from the time it opened. The bridge takes its name from two Carrara marble Medici lions that are copies of those found in the Loggia dei Lanzi in Florence, Italy; gifts of Andrew Anderson II, they represent Ponce de Leon which means “lion” in Spanish. After 80 years the bridge no longer met standards for ship impact and could not handle the city’s heaviest fire engine and required restoration. A temporary bridge was built to handle traffic and the Bridge of Lions closed for an $80 million rehabilitation. The work that modernized the bridge while sensitively preserving its historic character down to the original paint color won awards for the outfits involved.

TURN AND WALK OVER TO THE STATUE.  

16.
Ponce de Leon Statue
Charlotte Street between Cathedral Place and King Street

Andrew Anderson II was born in St. Augustine in 1839. Although his influential father died when he was only two young Anderson went on to be educated at Phillips Academy in Andover, Massachusetts, the oldest incorporated academy in the country, at a private school in Paris, France and at Princeton University. A Union sympathizer, he spent the Civil War in New York City but he returned to St. Augustine and immersed himself into the civic affairs of the town, so much so that he was elected mayor in 1886. In his later years he contributed public art to the St. Augustine streetscape including the marble lions at the base of the Bridge of Lions and this 4’ 11” life-size statue of Ponce de Leon, discover of Florida in 1513. It is an exact replica of the likeness that graces the explorer’s tomb in San Juan, Puerto Rico.

WALK UP INTO THE PARK. 

17.
Plaza de la Constitucion
Cathedral Street and King Street between Charlotte and St. George streets

This public space was established as a market area by edict of King Phillip II in 1598. In 1813 a pyramidal shaft was erected in the center as a monument to the adoption of the Spanish Constitution of 1812, from which the plaza takes its name. At the east end is an open, shed-like structure that dates to 1824 and hosted the occasional slave auction. Other historic sites on the plaza include an ancient public well and a monument to Confederate veterans.

EXIT THE PARK AT THE SOUTHEAST CORNER, FACING THE WATER. TURN RIGHT ON CHARLOTTE STREET. TURN RIGHT ON CADIZ STREET. TURN RIGHT ON AVILES STREET.

18.
Ximenez-Fatio House
20 Aviles Street

Aviles Street was the first street to be platted in America’s first city. Andres Ximenez, a shopkeeper, purchased this lot in 1797 and built a two-story house of coquina shellrock that featured a one-story wing of warehouses. For most of its 19th century life the structure served as a boarding house for Florida’s earliest tourists. For twenty of those years Louisa Fatio ran one of the town’s most desirable guest houses here. The property was purchased by the National Society of The Colonial Dames of America in 1939 and today operates as a house museum. The property, that includes a free-standing kitchen, is interpreted as an example of a pioneering woman-operated business. 

19.
Segui-Kirby Smith House
12 Aviles Street

This house from the late 1700s stands as one of only 36 houses remaining from the Spanish colonial era. In 1821, after he was named a United States District Judge, Joseph Lee Smith moved into the house from Connecticut. In 1824 his son Edmund Kirby was born here; the young Smith would graduate from West Point and distinguish himself in the Mexican-American War where his older brother, Captain Ephraim Kirby Smith, died in battle. During the Civil War Edmund Kibry Smith became one of only seven full generals in the Confederate Army. His command was west of the Mississippi and after the Confederacy fell he was cut off and would not surrender his army until June 2, 1865 in Galveston, Texas -  almost two months after Robert E. Lee’s surrender. Smith’s army was the last significant command in the field.

20.
Spanish Military Hospital Museum
3 Aviles Street

This reconstructed building was known as the Royal Hospital of our Lady Guadalupe when it operated during the second Colonial Spanish period from 1784 until 1821. Today it operates as a museum, interpreting the patient experience of 1791.

AT THE PLAZA, TURN LEFT ON KING STREET.

21.
Trinity Episcopal Church
215 South George Street at King Street

Trinity is the oldest Protestant church in Florida, established in 1821, with its first meetinghouse holding services in 1831. That small coquina building made it through the rest of 19th century before it was expanded into a muscular cruciform shape, retaining the original tower and some walls.

22.
Government House
10 Cathedral Placeat St. George Street

For more than 225 years, from 1595 until 1821, this was the site that served as headquarters for the Spanish, English and Spanish again territorial governors. The first house was sacked by English invaders in 1702 and when the Americans took over in 1821, they found little more than a shell of the Government House. Robert Mills, the first American-born professional architect, used the existing walls and fashioned a new building. Mills would later design the Washington Monument. Used as a museum today, the Government House seen today was rebuilt as a Depression-era project in the 1930s and used as a post office and customs house.

23.
Casa Monica Hotel
95 Cordova Street at King Street

Franklin Webster Smith was born into a prominent Beacon Hill family in Boston in 1826. Smith made his considerable fortune in the hardware trade but his passion was as a political reformer. He was an active abolitionist before the Civil War, founded the Boston YMCA and exposed corruption by public officials whenever he experienced it in his dealings with United States military. Smith’s in-laws built a summer home near St. Augustine after the war and he followed suit in 1883. Based on his extensive world travels, Smith pioneered the Moorish Revival style in town for his new home he called Villa Zorayda. He also innovated a building material of crushed coquina and Portland cement which he poured into casts. Across the country, building construction utilizing poured concrete would become all the rage and replaced more costly brick in many applications. After the success of his mansion, Smith set about building this hotel a block down the street in 1888. He named it Casa Monica after the African mother of St. Augustine, Bishop of Hippo. Smith turned out to be a much more successful architectural interpreter and builder than a hotelier and he quickly sold the property to Henry Flagler, who became enamored with Villa Zorayda while in St. Augustine on his honeymoon. Flagler operated the hotel as one of the three jewels of the Florida East Coast Railway Company’s St. Augustine operations. It was sold in 1961 to St. John’s County which used it as a courthouse for more than 30 years. Richard Kessler purchased the property in 1997 and restored it to its original purpose as a linchpin in his collection of boutique hotels.    

24.
Ponce de Leon Hotel (Flagler College)
74 King Street

This is the building on which Henry Morrison Flagler, a co-founded of Standard Oil, launched his Florida empire, establishing St. Augustine as a fashionable resort destination for travelers on his Florida East Coast Railway. Flagler borrowed the construction techniques his friend Franklin Smith used in his house across the street and the hotel became the first major building in America to be crafted using poured concrete. He hired Thomas Hastings and John M. Carrere, who would later design some of the country’s most elegant classical buildings, for their first major commission. They delivered a pioneering Moorish-style palace with tall spires, turrets and wide, red-tiled roofs. Louis Comfort Tiffany, fresh off his interior redesign of the White House, provided much of the interior elements that include Tiffany stained glass, imported marble and carved oak. Thomas Edison, a Flagler friend, made sure the entire hotel was wired for electricity when it greeted the first guests in 1887. In 1968 the hotel became the centerpiece of the newly-established Flagler College.

ACROSS THE STREET IS...

25.
Alcazar Hotel (City Hall)
75 King Street

Do you think lodgings at the Ponce de Leon Hotel might be out of your price range? This was Henry Flagler’s idea of a budget hotel. He set Thomas Hastings and John M. Carrere to work again in 1888 and they designed a facade modeled after a Morrish palace in southern Spain, decorated with generous amounts of terra cotta ornamentation. Inside guests could enjoy a steam room, sulphur baths and Florida’s first indoor swimming pool. Otto Curtis Lightner began his career setting newspaper type in Kansas and made his fortune turning arounddistressed publishing properties. His magazines and newspapers encouraged American to “have a hobby and collect something.” He practiced what he preached and filled several large estates in the Chicago area with his assemblies of Victorian memorabilia. In the 1940s he moved to St. Augustine to restore his health and while staying in the Ponce de leon Hotel decided to buy the old Alcazar Hotel for a reported $150,000 and deeded it to the city for use as a museum for his extensive collection of Victorian memorabilia. After a quarter century the remodeled building was dedicated as St. Augustine City Hall on April 27, 1973 and the Lightner Museum opened the following year. O.C. Lightner died in 1950 and is buried in the courtyard

26.
Villa Zorayda
83 King Street

This is the house built by Franklin Smith that helped popularize the construction method of poured concrete, caught Henry Flagler’s eye and helped lead him to Florida and set the groundwork forthe fanciful style of Florida architecture that came to be known as Mediterranean Style. In addition to its whimsical design, each window is of a slightly different shape and size, adhering to the superstition that it would allow spirits to leave the house but thwart their re-entry. Smith left St. Augustine for Saratoga Springs after he sold his Casa Monica Hotel, hoping to infuse that upstate New York gambling town with some cultural education but his grand vision was to makeover Washington, D.C., then little more than a provincial Southern town, into a grand cultural treasure that would include the best work from eight civilizations in history. That scheme and the Panic of 1893 caused Smith to go broke. The banks foreclosed on his properties in St. Augustine, Washington, D.C. and Saratoga Springs and Smith died in anonymity and poverty in 1911 at the age of 84. Villa Zorayda did duty as a speaeasy during Prohibition but today is completely renovated and open as a museum.

27.
Markland House
102 King Street

Andrew Anderson arrived in St. Augustine from New York in 1829 and quickly established himself as a leader in the church and community. He began work on this coquina shellstone mansion in 1939 in the center of an orange grove just two years before he died in the Yellow Fever epidemic of 1841. The Greek Revival house stayed in the family until 1924 when Andrew Anderson II died at the the age of 85. The mayor of St. Augustine, Herbert E. Wolfe bought the mansion and sold it to Flagler College in 1966. 

TURN RIGHT ON MARKLAND PLACE. TURN RIGHT ON VALENCIA STREET.

28.
Flagler Memorial Presbyterian Church
36 Valencia Street

This is the oldest Presbyterian congregation in Florida, formed in 1824 with twelve members. It was probably the church of Henry Flagler, the son of a Presbyterian minister, after he came to St. Augustine, although there is no direct evidence of that. In 1889 Flagler’s daughter Jennie Louise Benedict was living in New York City and preparing to give birth. Tragically the baby girl died a few hours after birth and Jennie barely survived the affair. On doctor’s orders she set sail for St. Augustine where it was hoped she would regain her strength. Instead, she died at sea and Henry Flagler met a yacht flying its flag at half mast. Flagler had met tragedy before; when his first wife died in 1881 he had built a classically artistic monument over her grave at the cost of $50,000. Flagler’s reaction to the loss of his daughter and granddaughter bewilders to this day. Rather than a monument he built this church - and a church like no other. The architects he had plucked from a small drawing room in the legendary firm of McKim, Mead and White, Thomas Hastings and John Carrere, were brought back to St. Augustine and they created a sanctuary that has been described as in the style of the Ventian Renaissance for its magnificent 100-foot copper dome that resembles the one in St. Mark’s Cathedral in Venice. The striking entrance facing Valencia Street, with three Venetian arches supported by red terra cotta Ionic pillars under a broad Roman arch, isn’t even the main entrance.   This grand church was dedicated on March 16, 1890 when the congregation totaled about 40 members. Although Henry Flagler would follow his Florida East Coast Railway down the coast to Palm Beach where he died in 1913 at the age of 83 after tumbling down the stairs in his Whitehall mansion, this is where he is buried. Beside him in the mausoleum are the remains of his first wife, Mary Harkness, his daughter Jennie and his granddaughter Margery.    

TURN LEFT ON CORDOVA STREET.

29.
Grace United Methodist Church
8 Carrerra Street at Cordova Street

Grace United Methodist Church began modestly in the parlors of the Old Florida House Hotel and before the decade was out would be worshiping in one of the finest church buildings in 19th century America. Pastor George Atkins of Asbury Park, New Jersey ministered to the tiny congregation in rooms around town until 1884 when the “Olivet Methodist Episcopal Church” building was constructed in 1884. Pews were made from construction material spread between nail kegs, and the windows were covered with muslin. It was shortly thereafter that Henry Flagler arrived in town with a vision for transforming St. Augustine into “the Newport of the South.” Part of that plan involved the land where the fledgling Olivet church building stood. As part of the deal to acquire that land for his Alcazar Hotel Flagler agreed to build the congregation a new church. Thomas Hastings and John Carrere were put to work once again and they designed an elegant Spanish Renaissance sanctuary that was dedicated in January 1888. Constructed of poured concrete like Flagler’s other buildings, the Grace United Methodist Church stands today much as it did 125 years ago.  

30.
Tolomato Cemetery
Cordova Street

Located just outside the city gates, this was a village for Indian converts to Christianity and the Franciscan monks who ministered to them. When the British took over in 1763 they dismantled the church for firewood. In the 1790s the grounds became a graveyard for Minorcan refugees from the failed settlement of New Smyrna. Burials, some in above-ground coquina crypts, took place until 1892. Like the nearby Huguenot Cemetery, this is a popular stop on St. Augustine ghost tours. Look for an appearance by the Ghost Bride, Elizabeth Forrester, who died on her wedding day in 1783 and was laid to rest in her wedding gown.

WALK A FEW MORE STEPS ON CORDOVA STREET TO THE TOUR STARTING POINT AT THE VISITOR CENTER.